[Boromir88]

Orcs are a much bigger can of worms to open at the moment, so I'll leave that be for now. I'll just say that I agree. I don't think there's anything, within the canon, to support orcs were capable of redemption. However, I do think having orcs be beyond redemption did bother Tolkien's Catholic beliefs.

They would be Morgoth’s greatest Sins, abuses of his highest privilege, and would be creatures begotten of Sin, and naturally bad (I nearly wrote ’irredeemably bad’; but that would be going too far. Because by accepting or tolerating their making - necessary to their actual existence - even Orcs would become part of the World, which is God’s and ultimatly good.)~Letter #153

Originally Posted by Morthoron

Did Sauron really consider being redeemed and beg forgiveness, or was it more a matter of being overawed by the Valar, and the utterly crushing defeat of Morgoth? I recall he was ordered to return to Valinor to face judgement, but he bided his time and basically hid himself away when the Valar took their eyes off the ball.

This is debatable. I recall Sauron suing for pardon from Eonwe (Eonwe, being recognized as the greatest of Sauron's order). Eonwe says it's not within his authority to pardon him, so he must go before the Valar. If I also recall correctly, Tolkien wrote Sauron didn't go because of his pride, which would suggest he wasn't in truth "redeemed", at least I don't think anyone could say in an official capacity.

With Boromir, I think it's far more clear cut. Boromir confesses his sins to Aragorn, Aragorn forgives them. And then later Gandalf after hearing Boromir's sins says (parahrasing here from The White Rider): "He escaped in the end. I am glad." This seems like an official pardoning, Boromir confesses to his king, the King and one of the Maiar declared Boromir's sins were forgiven.

This never officially happens with Sauron, but it doesn't necessarily mean he wasn't in truth, repentant for his sins committed under Morgoth.

He [Sauron] still had the relics of positive purposes, that descended from the good of the nature in which he began: it had been his virtue (and therefore also the cause of his fall, and of his relapse) that he loved order and co- ordination, and disliked all confusion and wasteful friction.~Morgoth's Ring

I think this suggests Sauron had 2 falls, because Sauron's "virtue" is what led to his initial fall (joining Morgoth), as well as the cause of his relapse (making the Rings of Power). "Relapse" - to me, suggests there was a period (however brief) Sauron was sincere in his efforts to heal Middle-earth after Morgoth's defeat.